Client Onboarding on Autopilot: Contracts, Invoices, Kickoff

Turning “yes” into revenue shouldn’t take a week. This guide shows how to automate e-sign contracts, invoices, intake forms, and your kickoff so new clients get value fast and you get paid on time—without code.

Table of Contents

• Who This Guide Is For
• Principles (Fast, Safe, and Consistent)
• Map the Flow (From “Yes” to Kickoff)
• Contract & Proposal: E-Sign Without Friction
• Invoicing & Payments: Cash In (Politely)
• Intake: Get What You Need Without Back-and-Forth
• Kickoff: Start With Value, Not Slides
• Field Map (Copy This to Your CRM)
• Comparison Table: Minimal vs Advanced Onboarding
• Starter Stacks (Copy & Adapt)
• Implementation Checklist
• 30-Day Rollout Plan
• Security, Privacy & Legal (Plain English)
• Templates You Can Copy
• KPIs Dashboard (Update Weekly)
• FAQs
• Internal Links (add them at the end)

Who This Guide Is For

Service entrepreneurs, agencies, and consultants who want a repeatable onboarding process: proposal → contract → invoice → intake → kickoff. You’ll get templates, field maps, guardrails, KPIs, and a 30-day plan, plus internal links to related posts for a complete stack.

If you still need the core stack, start with The Entrepreneur’s Automation Stack → /entrepreneurs-automation-stack. Pair this post with Bookkeeping on Autopilot → /automate-bookkeeping-entrepreneurs.

Principles (Fast, Safe, and Consistent)

• Template-first. Lock legal clauses. Only scope, timeline, and pricing change per client.
• One source of truth. CRM fields feed proposals, contracts, invoices, and kickoff tasks.
• Automate handoffs, not judgment. Humans approve discounts or unusual terms; automations handle creation, routing, and reminders.
• Evidence by default. Store consent, signatures, and approvals with timestamps.
• Security from day one. Least-privilege access, audit logs, and retention rules.

Map the Flow (From “Yes” to Kickoff)

1. Deal marked “Verbal Yes” in CRM → generate proposal/contract with client data.
2. Client e-signs → contract PDF saved to client folder; CRM stage set to Won.
3. Invoice auto-created and sent with payment link; reminders scheduled.
4. Intake form personalized and prefilled (where possible).
5. Kickoff checklist and calendar slot created; welcome email sent.
6. Project board and shared folder created with permissions.
7. First value delivered in <7 days (report, audit, roadmap, or install).

Contract & Proposal: E-Sign Without Friction

Goal: A signed contract within 24–48 hours.

Proposal/contract structure

• Overview: outcomes and value in 3–5 bullets.
• Scope: deliverables, responsibilities, acceptance criteria.
• Timeline: phases and key dates.
• Price & payment schedule: currency, due dates, late fees.
• Legal notes: IP, confidentiality, termination, liability (locked).
• Signature block: e-sign + timestamp.

Automation

• From CRM deal: populate client name, email, billing details, plan, start date.
• Generate proposal PDF + e-sign link.
• On signature: move stage → Won, post in Slack/Email, create invoice + kickoff tasks.

Guardrails

• Approval required for discount > X% or changes to locked legal.
• Versioning: ClientName_Contract_2025-01_v1.pdf.
• Store signed PDFs with metadata (deal ID, date).
• Legal reference on e-sign validity (see U.S. ESIGN Act overview: https://www.ftc.gov/business-guidance/resources/esign-act).

KPIs

• Time from “verbal yes” → signed.
• Abandoned contracts (sent, not signed) and main blockers.
• % contracts signed on first link (no revisions).

Invoicing & Payments: Cash In (Politely)

Goal: Invoice on signature and money in the bank on schedule.

Workflow

• On signature → create invoice (amount, due date, method) + send payment link.
• Schedule reminders: 3 days before due, due day, +7 days.
• On payment → receipt + project starts; update DSO dashboard.

Best practices

• Offer two methods (card + bank transfer).
• Add late-fee policy and discount for early payment (optional).
• Split large projects into milestones (deposit, mid-project, delivery).

KPIs

• DSO (Days Sales Outstanding).
• % invoices paid on time.
• Time from signature → first payment.

When you scale, connect this with your monthly pack (see Reporting on Autopilot) → /automate-reporting-dashboards.

Intake: Get What You Need Without Back-and-Forth

Goal: Collect the minimum set of inputs to start delivering within 7 days.

Intake form sections

• Access & accounts: URLs, logins via secure share, permission contacts.
• Brand & assets: logo, fonts, brand voice, examples to mimic/avoid.
• Product & ICP: offers, pricing, ideal customer, key objections.
• Current stack: domains, analytics IDs, CRM, helpdesk, CMS.
• Success criteria: “In 30 days, success looks like…”.

Automation

• Prefill known fields from CRM (name, company, site).
• Conditional questions by plan or service.
• On submit → create checklist with tasks per field and notify owner.

Guardrails

• Avoid collecting sensitive IDs in plain text; use a secure upload/request link.
• Keep PII only where needed; set retention.

Kickoff: Start With Value, Not Slides

Goal: Deliver a tangible first win quickly.

Kickoff agenda (45–60 min)

1. Quick outcomes recap and KPIs.
2. Confirm access and roles; define owner for each input.
3. Present first 7-day deliverable (audit, one quick fix, or content pack).
4. Risks & dependencies; communication cadence; next milestone.

Automation

• Create calendar event with agenda + doc links.
• Generate project board (To Do / Doing / Done) with prefilled tasks.
• Send welcome email with links, schedule, and support channel.

KPIs

• Kickoff booked within 3 business days of signature.
• % completed inputs from intake by Day 3.
• First deliverable shipped by Day 7.

Field Map (Copy This to Your CRM)

• Client: company, website, billing email, legal name.
• Deal: plan/tier, scope summary, start date, price, payment schedule.
• Finance: invoice ID, due date, paid date, method.
• Delivery: project board URL, shared folder URL, owner, SLA.
• Compliance: contract URL, signature date/time, retention window.

Comparison Table: Minimal vs Advanced Onboarding

Area	Minimal (Week 1–2)	Advanced (Month 2–3)	KPI
Proposal & Contract	One template + e-sign	CPQ rules, multi-currency	Time to sign
Invoicing	Invoice on sign + reminders	Milestones, subscriptions	DSO
Intake	Prefilled form	Conditional paths, secure vault	Inputs by Day 3
Kickoff	Agenda + checklist	Auto project board + SOPs	Day 7 deliverable
Evidence	Store PDFs & timestamps	SIEM/log export, retention	Audit readiness

Starter Stacks (Copy & Adapt)

“Deposit Today”

• Contract e-sign → auto-invoice deposit
• Payment link + reminders
• Kickoff scheduler with buffers
• KPI: time from yes → paid

“Inputs in 48 Hours”

• Prefilled intake form
• Task creation per field
• Daily reminder (3 days max)
• KPI: % inputs complete by Day 3

“Ship First Value”

• Project board template + SOP
• Welcome email with links
• Deliverable due Day 7
• KPI: client NPS after week 1

Implementation Checklist

• Lock proposal/contract templates; version control.
• Connect CRM → e-sign → invoicing.
• Create intake form with conditional logic and secure file requests.
• Build kickoff checklist and project board template.
• Enable audit logs and set data retention.
• Weekly KPI snapshot: time to sign, DSO, inputs Day 3, first deliverable Day 7.

30-Day Rollout Plan

Week 1 — Map & Templates: draft proposal/contract, invoice, intake, kickoff checklist. Baseline time to sign and DSO.
Week 2 — Wire & Pilot: connect CRM→e-sign→invoice; launch intake; schedule two kickoffs.
Week 3 — Iterate: reduce fields, clarify scope language, split payments if needed, shorten kickoff.
Week 4 — Prove & Decide: 1-pager with before/after KPIs + screenshots. Scale or adjust.

Security, Privacy & Legal (Plain English)

• Use least-privilege access for contractors.
• Avoid storing passwords in notes; use a password manager or secure vault link.
• Keep signed docs and consents with timestamps.
• Respect PII and client data retention periods.
• E-sign is legally binding in many regions (see ESIGN link above) and eIDAS in the EU; store the audit trail.

Templates You Can Copy

Welcome Email (Post-Signature)
“Great to have you on board, [Name]! We’ve queued your kickoff for next week. Here’s what to expect:

1. Contract + invoice receipts (attached).
2. A short intake form (5–7 minutes) so we can hit the ground running.
3. A 45-min kickoff where we confirm access and deliver your first quick win.
   Links: [Intake], [Kickoff scheduler], [Shared folder].
   If anything’s urgent, reply to this email—our team is on it.”

Scope Box (Proposal Template)

• Deliverables: list items with acceptance criteria.
• Out of scope: 3–5 lines to prevent surprises.
• Dependencies: client access, assets, approvals.
• Change requests: how to price or handle.

KPIs Dashboard (Update Weekly)

• Time from verbal yes → signed
• DSO and % on-time payments
• Intake completion by Day 3
• Kickoff booked within 3 days
• First deliverable shipped by Day 7
• Client NPS after first week

FAQs

Can I skip proposals and send a contract only?
For small engagements, yes—combine proposal and contract to reduce friction.

What if clients delay the intake?
Shorten the form to the essentials and send daily reminders for 3 days. Offer to fill it together in the kickoff.

Deposit or net-30?
For small businesses, start with deposit up-front. Add milestones for larger scopes.

Who should own onboarding?
You, until revenue allows a part-time ops role. The process remains the same.

Internal Links (add them at the end)

• /entrepreneurs-automation-stack
• /automate-lead-capture-nurture
• /inbox-calendar-automation-founders
• /automate-bookkeeping-entrepreneurs
• /automate-reporting-dashboards
• /legal-security-automation-small-biz